Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux

Angers, France

Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux

Angers, France
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Bertrand S.,Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux | Duval O.,Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux | Helesbeux J.-J.,Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux | Larcher G.,Groupe dEtude des Interactions Hote Parasite | Richomme P.,Laboratoire des Substances dOrigine Naturelle et Analogues Structuraux
Tetrahedron Letters | Year: 2010

The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of Nα-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from l-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone. © 2010 Elsevier Ltd. All rights reserved.

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